Organic synthesis is of crucial importance for biomedical and pharmaceutical research. Synthesis of natural products and other biologically important organic molecules relies on a toolbox of methods and reagents allowing selective construction and structural modification of complex organic molecules. Oxidative modification of organic compounds is one of the cornerstones of modern synthetic methodology. Our research in general is aimed at the development of new synthetic methodologies based on the organic chemistry of main-group elements. In the last few years we succeeded in the preparation of several new, potentially useful classes of polyvalent iodine compounds. Among these new compounds, the most promising are the amino acid based benziodazoles, which are powerful and selective oxidizing reagents analogous to the widely used Dess-Martin periodinane. Moreover, our new oxidizers have several advantages over the existing reagents. Specifically, they have a longer shelf life compared to Dess-Martin periodinane, and they can be used as enantioselective oxidizers in asymmetric syntheses. Based on these preliminary results, we propose to develop a series of oxidizing reagents that are useful in the synthesis of biologically important organic molecules. Within the above context our specific objectives for this grant period are: (1) Development of new iodine(V) based oxidizing reagents- analogs of Dess-Martin periodinane (2) Development of new reagents and synthetic methods for oxidative azidation, amidation, and cyanation of organic substrates. (3) Evaluation of all new compounds and their derivatives as potential antitumor agents. One of the main objectives of our research program is to provide excellent training in science to pre-medical and pre-pharmacy B.S. and M.S. students and to further strengthen undergraduate and graduate research programs at the University of Minnesota Duluth. It is important to emphasize that this research will be performed by undergraduate and graduate research assistants. The educational goals of this proposal are to continue to strengthen the learning aspects of scientific research and those related to the integration of research and education. This proposal and this university provide the appropriate means for strengthening and developing critical thinking, fostering curiosity, and sharing the excitement of discovery.